There are many different ways to break in a new baseball glove. Some make sense, others are just plain silly. I have broken in several gloves over the years, and even screwed up a couple times. Although, never seriously enough that the glove became useless for play. Here is my philosophy for breaking in a new baseball or softball glove.
Breaking in a new glove requires patience and it may take 1/2 of a playing season or more before the new glove sees game action. I generally use the "new" glove in the outfield while shagging balls during BP, and take ground balls in the infield once I have completed the preliminary "break-in" steps described below:
(1) Unwrap the glove and put it on your hand. Fold the glove across the hinge with your throwing hand several times.
(2) Go out and play catch with the glove each day. Continue flexing the glove across the hinge in between throws while you are playing catch. Have fun and talk with your partner while you build arm strength to play ball, and break in your new glove. If you can find a partner that throws hard, your glove will break in faster and you will get better at playing catch!
(3) If you must use a glove conditioner, use Lexol leather conditioner. It is impossible to use too much. It provides adequate lubrication to the leather fibers, and it does not soak in and make the glove padding heavy.
Put a small amount of Lexol on a clean sponge or rag and rub it into the triangle formed between the base of the web and the hinge at the heel of the glove.
Continue to flex the glove across the hinge while wearing it. This will help the glove conform to the anatomy of "your" hand and give you a custom fit.
(4) Finally, I store all of my gloves on a shelf in the house and use the Glove Guard to help them retain their shape. Of course, a baseball or softball in the pocket also works to keep the glove from becoming a flattened pancake
Use the following procedure to keep your glove in top playing condition.